N-Acetyllactosamine (LacNAc) Production Service
As a natural prebiotic, LacNAc plays an important role in the regulation of the intestinal microbial environment. CD BioGlyco supplies suitable synthesis methods to achieve efficient production of LacNAc.
LacNAc as Natural Prebiotics
LacNAc (Galβ1, 4GlcNAc) is present in human milk as a free disaccharide. This compound is an important component of human milk oligosaccharides (HMOs). It has repetitive and variable branched lactose and/or LacNAc units, usually linked to sialic acid and fucose monosaccharides.
Human glycohydrolases do not degrade most HMOs, indicating that these structures have evolved into natural prebiotics to drive the correct assembly of healthy infant intestinal microbiota. LacNAc has been proven to be the major bifidogenic factor in the 1950s. Some HMOs contain lactose (Galβ1-4Glc) at their reducing ends, which can be added β1-3- or β1-6-linked lacto-N-biose (Galβ1-3GlcNAc) or LacNAc. Then, Lactose or oligosaccharide can be fucosylated by fucosyltransferases in α1-2, α1-3, or α1-4 linkage and/or sialylated by sialyltransferases in α2-3 or α2-6 linkage to produce various terminal structures. Yoshida et al. characterized the β-galactosidase of Bifidobacterium longum subsp. infantis to determine how the organism degrades type-1 (lactose-N-disaccharide) and type-2 (LacNAc) isomers of HMOs.
LacNAc Involved in Life Activities
LacNAc is a constituent of glycoproteins and glycolipids in the gastrointestinal tract. These backbones are used to connect core structures, which are directly attached to proteins or lipid aglycones with terminal sugars. LacNAc building blocks and terminal sugars also act as important precursors of a variety of blood type epitopes (Lewis A, Lewis B, sialyl Lewis A), and they participate in biological processes, including fertilization, the mediation of cell adhesion, and the adhesion of pathogens to colon cells.
Common Synthetic Methods of LacNAc
LacNAc itself can act as a natural prebiotic and as a building block for the production of various bioactive oligosaccharides, especially since this synthesis can be used to increase the value of lactose in dairy products. Chemical and enzymatic synthetic processes are the most commonly evaluated methods for LacNAc production. Compared with enzymatic synthesis, the yield of LacNAc produced by chemical synthesis is lower, which has more disadvantages in industrial production. In recent years, glycoside hydrolases and β-galactosidases with hydrolytic and transglycosylation activities have received special attention for the regioselective and stereoselective synthesis of LacNAc oligosaccharides.
LacNAc Production Service at CD BioGlyco
CD BioGlyco provides a variety of methods to produce LacNAc. Among them, enzymatic synthesis is the most suitable method for the large-scale production of LacNAc. Our researchers will further focus on robust enzyme development and reaction technology optimization to achieve large-scale production of LacNAc and its derivative oligosaccharides. Our Technologies for HMO Production include but are not limited to the following:
- Enzymatic synthesis
- Enzymes obtained from bacteria, fungi, and yeast are used to synthesize LacNAc and related derivatives.
- The enzymes responsible for the formation of new glycosidic bonds fall into two classes: glycoside hydrolases and glycosyltransferases with transglycosylation capabilities.
- Generating enzyme variants to optimize reactions.
- Microbial Fermentation
A complete and mature service product line from strain development to mass manufacturing.
Workflow
Publication Data
Journal: Molecules
IF: 4.6
Published: 2017
Results: This article presents the first reported enzymatic synthesis of LacNAc type 1 oligomers and their characterization as multivalent ligands for galectins. The researchers used two recombinant Leloir-glycosyltransferases—β1,3-galactosyltransferase and β1,3-N-acetylglucosaminyltransferase—in both sequential and one-pot approaches to synthesize LacNAc type 1 oligomers. Enzyme-linked lectin assays (ELLA) investigated the binding of these neo-glycoproteins to full-length tumor-associated human galectin-3 (Gal-3) and its truncated counterpart Gal-3Δ (lacking N-terminal residues 1–62). Key findings included a significantly higher binding affinity of Gal-3Δ for the neo-glycoprotein presenting LacNAc type 1 repeating units, marking the first evidence of differential glycan selectivity between Gal-3Δ and Gal-3. The study concludes that LacNAc type 1-presenting neo-glycoproteins hold potential for tracing Gal-3Δ during tumor progression and therapy.
Fig.1 One-pot synthesis of LacNAc type 1 glycan oligomers 2-5. (Fischöder, et al., 2017)
Advantages
Advanced Chemoenzymatic Purity
Our state-of-the-art chemoenzymatic approach enables the production of highly purified LacNAc with meticulous stereochemical control, effectively preventing the formation of undesirable byproducts commonly seen in conventional synthesis methods.
Decades of Glyco-Expertise
Composed of preeminent glyco-experts with decades of cumulative experience in carbohydrate chemistry and glycoengineering, our team possesses the technical depth to resolve complex challenges and deliver custom-tailored solutions for even the most ambitious projects.
Rigorous Analytical Validation
Each batch of LacNAc undergoes a comprehensive suite of analytical evaluations to ensure compliance with our rigorous quality benchmarks, guaranteeing a reliable product that is immediately ready for your specific applications.
Applications
Nutrition and Functional Foods
LacNAc is essential for developing infant formulas and functional food products that support a healthy gut microbiota and bolster the immune system.
Glycoconjugate Drugs and Vaccines
LacNAc serves as a key component in the synthesis of glycoconjugate drugs and vaccines. Its role in cell-cell recognition and as a ligand for lectins makes it a valuable target for drug discovery.
Disease Diagnostics and Biomarker Development
LacNAc-containing probes and glycoconjugates are used as biomarkers for various diseases. High-purity LacNAc is a necessary component for developing reliable diagnostic assays.
Fundamental Glycobiology Research
Researchers utilize LacNAc as a fundamental tool to study complex biological processes, including cell adhesion, signal transduction, and host-pathogen interactions.
Frequently Asked Questions
Customer Review
"The quality of the LacNAc provided by CD BioGlyco was exceptional, which significantly streamlined our NMR studies of galectin-glycan interactions. The detailed MS and NMR data provided in the CoA gave us immediate confidence to move forward with our critical experiments, saving us weeks of purification and validation time."
- Dr. J.R., Lead Glycochemist
"We needed kilogram quantities of type 2 LacNAc for an HMO precursor project, and CD BioGlyco's pricing, driven by their enzyme regeneration system, was unmatched. Their ability to rapidly scale production while maintaining consistent quality across batches was a game-changer for our manufacturing timeline."
- A.P., Director of Process Development
"Our project required custom LacNAc derivatives with a specific functional tag for bioconjugation to an antibody. CD BioGlyco successfully synthesized the precise molecule and delivered it ahead of schedule. Their technical communication regarding the synthesis pathway and quality control checkpoints was clear and transparent throughout the entire engagement."
- S.C., Principal Investigator, Immunobiology Laboratory
Associated Services
At CD BioGlyco, our expertise extends far beyond single-molecule production. We offer a suite of complementary services designed to support your entire glyco-related project lifecycle. To get the most out of your LacNAc production service, consider these related offerings:
- Carbohydrate Synthesis: We provide a comprehensive glycan synthesis service to help you build complex carbohydrate structures using our high-purity LacNAc.
- Glycan Analysis and Profiling: Ensure the success of your research with our advanced glycan analysis services, which provide detailed structural characterization and profiling of your samples.
- Protein Glycosylation Analysis: For projects focused on glycoproteins, our protein glycosylation analysis service provides critical insights into the site-specific glycosylation of your protein of interest.
CD BioGlyco made many achievements in the field of production services of LacNAc, which are widely praised by clients internationally. If you have any further queries, please contact us directly for more details.
Reference
- Fischöder, T.; et al. Enzymatic synthesis of N-acetyllactosamine (LacNAc) type 1 oligomers and characterization as multivalent galectin ligands. Molecules. 2017, 22(8), 1320. (Open Access)
